Nafcillin

Nafcillin

File:Nafcillin.svg
Systematic (IUPAC) name
(2S,5R,6R)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a685019
Pregnancy category	US: B (No risk in non-human studies)
Legal status	℞ (Prescription only)
Routes of administration	IM, IV
Pharmacokinetic data
Protein binding	90%
Metabolism	<30% hepatic
Biological half-life	0.5 hours
Excretion	Biliary and renal
Identifiers
CAS Number	985-16-0 Y
ATC code	J01CF06 (WHO)
PubChem	CID: 8982
DrugBank	DB00607 Y
ChemSpider	8634 Y
UNII	SY07234TTS Y
ChEBI	CHEBI:7447 Y
ChEMBL	CHEMBL1443 Y
Chemical data
Formula	C21H22N2O5S
Molecular mass	414.476 g/mol
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c1ccccc1ccc2OCC)[C@H]4SC3(C)C
InChI InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1 Y Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N Y
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Nafcillin sodium is a narrow-spectrum beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

Nafcillin is considered therapeutically equivalent to oxacillin, although its safety profile is somewhat different.

Indications

Nafcillin is indicated in the treatment of staphylococcal infections, except those caused by MRSA.

U.S. clinical practice guidelines recommend either nafcillin or oxacillin as the first-line treatment of choice for staphylococcal endocarditis in patients without artificial heart valves.

Side-effects

As with all penicillins, serious life-threatening allergic reactions can occur.

Milder side-effects include:

• Hypokalemia
• Nausea and vomiting
• Diarrhea, often due to suppression of normal gastrointestinal bacteria, which, on occasion, leads to a more serious super-infection with an organism like Clostridium difficile
• Abdominal pain
• Yeast infections (thrush) affecting the mouth and tongue or vagina
• Agranulocytosis, neutropenia

Interactions

There is evidence that it induces cytochrome P-450 enzymes specifically CYP2C9.

The other aspect of this medication is that this medication contains lots of salts as media. So it could cause some edema or fluid accumulation. It would be prudent to avoid this medication if there were a concern for a congestive heart failure or kidney disease.